Technology Process of (-)-14-benzylidene-(15S)-hydroxy-(6S,13R,19R)-trimethyl-(9R)-propyl-8,20-dioxabicyclo[15.2.1]icosan-7,11-dione
There total 18 articles about (-)-14-benzylidene-(15S)-hydroxy-(6S,13R,19R)-trimethyl-(9R)-propyl-8,20-dioxabicyclo[15.2.1]icosan-7,11-dione which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
- Guidance literature:
-
With
bis(1,5-cyclooctadiene)nickel (0); triethyl borane; tributylphosphine;
In
toluene;
at 60 ℃;
for 14h;
DOI:10.1021/ja042733f
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 69 percent / PPh3 / CH2Cl2 / 16 h / 23 °C
2.1: MeLi / diethyl ether / 1.5 h / -78 °C
2.2: 92 percent / tetrahydrofuran; diethyl ether / -78 - 20 °C
3.1: 45 percent / Ni(cod)2; PBu3; Et3B / 14 h / 23 °C
4.1: 80 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 0 °C
5.1: 86 percent / Pd(PPh3)4; CuI; pyrrolidine / 16 h / 20 °C
6.1: 72 percent / dicyclohexylcarbodiimide; 4-pyrrolidinopyridine / CH2Cl2 / 14 h / 23 °C
7.1: ozone / CH2Cl2 / -78 °C
7.2: Me2S / CH2Cl2 / 3 h / -78 - 20 °C
7.3: 80 percent / PPh3 / CH2Cl2 / 0.67 h
8.1: 58 percent / Ni(cod)2; PBu3; Et3B / toluene / 14 h / 60 °C
With
pyrrolidine; bis(1,5-cyclooctadiene)nickel (0); copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethyl borane; tributylphosphine; tetrabutyl ammonium fluoride; methyllithium; 4-pyrrolidin-1-ylpyridine; ozone; dicyclohexyl-carbodiimide; triphenylphosphine;
In
tetrahydrofuran; diethyl ether; dichloromethane; toluene;
5.1: Sonogashira coupling;
DOI:10.1021/ja042733f
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: MeLi / diethyl ether / 1.5 h / -78 °C
1.2: 92 percent / tetrahydrofuran; diethyl ether / -78 - 20 °C
2.1: 45 percent / Ni(cod)2; PBu3; Et3B / 14 h / 23 °C
3.1: 80 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 0 °C
4.1: 86 percent / Pd(PPh3)4; CuI; pyrrolidine / 16 h / 20 °C
5.1: 72 percent / dicyclohexylcarbodiimide; 4-pyrrolidinopyridine / CH2Cl2 / 14 h / 23 °C
6.1: ozone / CH2Cl2 / -78 °C
6.2: Me2S / CH2Cl2 / 3 h / -78 - 20 °C
6.3: 80 percent / PPh3 / CH2Cl2 / 0.67 h
7.1: 58 percent / Ni(cod)2; PBu3; Et3B / toluene / 14 h / 60 °C
With
pyrrolidine; bis(1,5-cyclooctadiene)nickel (0); copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethyl borane; tributylphosphine; tetrabutyl ammonium fluoride; methyllithium; 4-pyrrolidin-1-ylpyridine; ozone; dicyclohexyl-carbodiimide;
In
tetrahydrofuran; diethyl ether; dichloromethane; toluene;
4.1: Sonogashira coupling;
DOI:10.1021/ja042733f
![(-)-(2S)-methyl-6-[(3S)-methyl-(5R)-(2-oxoethyl)tetrahydrofuran-(2S)-yl]hexanoic acid (5R)-methyl-3-oxo-7-phenyl-(1R)-propylhept-6-ynyl ester](/Databaselist/images/loading.webp)
